Fungicide pyridinyloxy substituted phenylamidine derivatives

Abstract

The present invention relates to 2,5-di-substituted-4-pyridinyloxy-substituted-phenyl-amidine derivatives, notably to 2,5-dialkyl-4-pyridinyloxy-substituted-phenyl-amidine derivatives, of formula (I) in which the substituents are as in the description, their process of preparation, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions (I).

1. A phenyl-amidine derivative of formula (I): 
       
         
           
           
               
               
           
         
         wherein
 R 1  represents H, a substituted or non substituted C 1 -C 12 -alkyl, a substituted or non substituted C 2 -C 12 -alkenyl, a substituted or non substituted C 2 -C 12 -alkynyl, SH or a substituted or non substituted S—C 1 -C 12 -alkyl; 
 R 2  represents a substituted or non substituted C 1 -C 12 -alkyl; 
 R 3  represents a substituted or non substituted C 2 -C 12 -alkyl, substituted or non substituted C 3 -C 6 -cycloalkyl, substituted or non substituted C 2 -C 12 -alkenyl, substituted or non substituted C 2 -C 12 -alkynyl, halogeno-C 1 -C 12 -alkyl; or 
 R 1  and R 2 , R 1  and R 3  or R 2  and R 3  can form together a substituted or non substituted 5 to 7-membered heterocycle; 
 R 4  represents a substituted or non substituted C 1 -C 12 -alkyl, a halogen atom, halogeno-C 1 -C 12 -alkyl, substituted or non substituted O—C 1 -C 12 -alkyl or cyano; 
 R 5  represents H, a substituted or non substituted C 1 -C 12 -alkyl, a halogen atom, halogeno-C 1 -C 12 -alkyl, substituted or non substituted O—C 1 -C 12 -alkyl or cyano; 
 m represents 1, 2, 3 or 4; 
 R 6  represents H, halogen, cyano, substituted or non substituted phenoxy, substituted or non substituted phenyl, substituted or non substituted C 1 -C 12 -alkyl, or halogeno-C 1 -C 12 -alkyl, NR 7 R 8 , OR 7 , SR 7 , trialkysilyl, COOR 7 , C(R 7 )═NOR 8 ; 
 R 7 , R 8  represent H, substituted or non substituted C 1 -C 12 -alkyl, aryl; 
 R 7  and R 8  may form a substituted or non substituted, saturated or non saturated 5- to 7-membered heterocycle; 
 
         as well as a salt; N oxide, metallic complex, metalloidic complex and/or optically active or geometric isomer thereof. 
       
     
     
       2. A compound of formula (I) according to  claim 1  wherein
 R 1  represents H, C 1 -C 12 -alkyl or SH; or 
 R 2  represents methyl or ethyl; or 
 R 3  represents C 2 -C 12 -alkyl, C 2 -C 12 -alkenyl or C 3 -C 6 -cycloalkyl; or 
 R 2  and R 3  can form together a substituted or non substituted 5- to 7-membered heterocycle; or 
 R 4  represents C 1 -C 12 -alkyl or a halogen atom; or 
 R 5  represents a C 1 -C 12 -alkyl or a halogen atom; or 
 R 6  represents H, a halogen atom, cyano, substituted or non substituted C 1 -C 12 -alkyl, or halogeno-C 1 -C 12 -alkyl, NR 7 R 8 , OR 7 , SR 7 , COOR 7 ; or 
 R 7  and R 8  independently represent H, methyl, ethyl, substituted phenyl; or 
 R 7  and R 8  may form a substituted or non substituted, saturated or non saturated 5- to 7-membered heterocycle; 
 as well as a salt, N-oxide, metallic complex, metalloidic complex and/or optically active or geometric isomer thereof. 
 
     
     
       3. A compound of formula (I) according to  claim 1  wherein
 R 1  represents C 1 -C 12 -alkyl; or 
 R 3  represents a non substituted C 2 -C 4 -alkyl, C 3 -C 4 -alkenyl or cyclopropyl; or 
 R 2  and R 3  can form together a 6-membered heterocycle; or 
 R 4  represents a non substituted C 1 -C 12 -alkyl or a chlorine atom; or 
 R 5  represents a non substituted C 1 -C 12 -alkyl or a chlorine atom; or 
 R 7  and R 8  may form a piperidinyl or a morpholinyl; 
 as well as a salt, N-oxide, metallic complex, metalloidic complex and/or optically active or geometric isomer thereof. 
 
     
     
       4. A compound of formula (I) according to  claim 1  wherein
 R 1  represents methyl or ethyl; or 
 R 3  represents ethyl, n-propyl, i-propyl, propenyl or allyl; or 
 R 2  and R 3  can form together a piperidinyl or a pyrrolidinyl; or 
 R 4  represents methyl or ethyl; or 
 R 5  represents methyl or ethyl; 
 as well as a salt, N-oxide, metallic complex, metalloidic complex and/or optically active or geometric isomer thereof. 
 
     
     
       5. A compound of formula (I) according to  claim 1  wherein R 2  and R 3  form together a bis-alkylated-pyrrolidinyl, as well as a salt, N-oxide, metallic complex, metalloidic complex and/or optically active or geometric isomer thereof. 
     
     
       6. A compound of formula (I) according to  claim 5  wherein R 2  and R 3  form together a bis-methyl-pyrrolidinyl, as well as a salt, N-oxide, metallic complex, metalloidic complex and/or optically active or geometric isomer thereof. 
     
     
       7. A process for the preparation of a compound of formula (I) according to  claim 1  comprising the following steps: 
       
         
           
           
               
               
           
         
       
     
     
       8. A method for controlling phytopathogenic fungi of crops, comprising applying an agronomically effective and substantially non-phytotoxic quantity of a compound according to  claim 1  to soil where a plant grows or is capable of growing, and/or to leaves and/or fruit of a plant or to a seed of a plant. 
     
     
       9. A compound of formula (I) according to  claim 1  wherein
 R 1  represents H, or a substituted or non substituted C 1 -C 12 -alkyl; 
 R 2 , R 3 , R 4 , and R 5  represent, independently, a substituted or non substituted C 1 -C 12 -alkyl; 
 R 6  represents H, halogen, substituted or non substituted C 1 -C 12 -alkyl, or halogeno-C 1 -C 12 -alkyl; and 
 m represents 1 or 2; 
 as well as a salt, N-oxide, metallic complex, metalloidic complex and/or optically active or geometric isomer thereof. 
 
     
     
       10. A compound of formula (I) according to  claim 1  wherein
 R 1  represents H; 
 R 2 , R 3 , R 4 , and R 5  represent, independently, methyl, ethyl, n-propyl, or i-propyl; 
 R 6  represents bromo, chloro, methyl, ethyl, i-propyl, or —CF 3 ; and 
 m represents 1 or 2; 
 as well as a salt, N-oxide, metallic complex, metalloidic complex and/or optically active or geometric isomer thereof. 
 
     
     
       11. A compound of formula (I) according to  claim 1  wherein
 R 1  represents H; 
 R 2 , R 4 , and R 5  represent methyl; 
 R 3  represents ethyl, n-propyl, or i-propyl; 
 R 6  represents: at position 2, H, bromo, chloro, methyl, ethyl, or i-propyl; at position 3, H, chloro, or —CF 3 ; at position 4, H, chloro, or —CF 3 ; at position 5, H or chloro; at position 6, H or methyl; or combinations thereof; and 
 m represents 1 or 2; 
 as well as a salt, N-oxide, metallic complex, metalloidic complex and/or optically active or geometric isomer thereof. 
 
     
     
       12. A compound of formula (I) according to  claim 1  wherein
 R 1  represents H; 
 R 2 , R 4 , and R 5  represent methyl; 
 R 3  represents ethyl, n-propyl, or i-propyl; 
 R 6  represents: 2-chloro-4-trifluoromethyl; 2-chloro-3-trifluoromethyl; 2-methyl-4-chloro; 2-ethyl-3-chloro; 2-ethyl-4-chloro; 2-isopropyl-4-chloro; 3-chloro-5-chloro; 2-chloro; 2-bromo; or 6-methyl; and 
 m represents 1 or 2; 
 as well as a salt, N-oxide, metallic complex, metalloidic complex and/or optically active or geometric isomer thereof. 
 
     
     
       13. A compound of formula (I) according to  claim 1  wherein
 R 1  represents H; 
 R 2 , R 4 , and R 5  represent methyl; 
 R 3  represents ethyl; 
 R 6  represents 2-bromo; and 
 m represents 1; 
 as well as a salt, N-oxide, metallic complex, metalloidic complex and/or optically active or geometric isomer thereof.